Glycine, N-methyl-, hydrochloride (1:1) → N-(4-(3-((4-Fluorophenyl)(isopropyl)amino)propyl)benzyl)-2,2-dimethyl-1,3-dioxan-5-amine

HRID 2046073Notes

Reaction equation

HRID 2046073 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:20]([CH3:22])[CH3:21])[CH2:9][CH2:10][CH2:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[CH3:23][C:24]1([CH3:31])[O:29][CH2:28][CH:27]([NH2:30])[CH2:26][O:25]1.FC1C=CC(N(CC2SC(C3C=CC(C=O)=CC=3)=CC=2)C(C)C)=CC=1.Cl.N(CC(O)=O)C>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:20]([CH3:22])[CH3:21])[CH2:9][CH2:10][CH2:11][C:12]2[CH:19]=[CH:18][C:15]([CH2:16][NH:30][CH:27]3[CH2:28][O:29][C:24]([CH3:31])([CH3:23])[O:25][CH2:26]3)=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 69483Glycine, N-methyl-, hydrochloride (1:1)HCID 117686082,2-Dimethyl-1,3-dioxan-5-amineHCID 866606094-(3-((4-Fluorophenyl)(isopropyl)amino)propyl)benzaldehydeHCID 866606114-(5-(((4-Fluorophenyl)(isopropyl)amino)methyl)thiophen-2-yl)benzaldehyde

Product 1

HCID 66614918N-(4-(3-((4-Fluorophenyl)(isopropyl)amino)propyl)benzyl)-2,2-dimethyl-1,3-dioxan-5-amineYield 48%

Procedure

When the product of Step C and 2,2-dimethyl-1,3-dioxan-5-amine were substituted for 4-(5-(((4-fluorophenyl)(isopropyl)amino)methyl)-thiophen-2-yl)benzaldehyde and sarcosine hydrochloride in Example 22, Step C, the similar process afforded the title compound in 48% yield, as creamy paste. 1H-NMR (CDCl3) 7.24 (d, 2H, J=7.92 Hz), 7.11 (d, 2H, J=7.92 Hz), 6.87 (t, 2H, J=8.9 Hz), 6.69-6.62 (m, 2H), 3.95 (dd, 2H, J=11.7, 3.6 Hz), 3.83-3.69 (m, 4H), 3.06 (t, 2H, J=7.54 Hz), 2.66-2.58 (m, 3H), 1.83-1.76 (m, 3H), 1.41 (s, 3H), 1.4 (s, 3H), 1.08 (d, 2H, J=6.59 Hz).

Sources & evidence

ORD record
ord-f0c603b434b54c3e806beb6f2ef21fef
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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